A comparative investigation for identification of N-(4-dimethylamino 3,5-dinitrophenyl)maleimide

Seda Karaboğa; Gürcan Yıldırım

doi:10.54187/jnrs.1241130

EN

A comparative investigation for identification of N-(4-dimethylamino 3,5-dinitrophenyl)maleimide

Abstract

This study has identified the characteristic behaviors of N-(4-dimethylamino 3,5-dinitrophenyl)maleimide molecule using ab initio Hartree-Fock (HF) and density functional theory (DFT) based on Becke’s three-parameter hybrid exchange functional combined with Lee-Yang-Parr non-local correlation function (HF/B3LYP and DFT/B3LYP) at 6-311G++(d,p) level of theory for the first time. On this basis, the optimized molecular structures, some thermodynamic features at 300 K, function groups of structures, charge distributions-dipole moments, molecular charge transfer regions, spectroscopic characteristic properties, vibrational frequencies, nuclear magnetic resonance chemical shifts of 13C-NMR and 1H-NMR spectra, and corresponding vibrational assignments have been investigated in detail. Comparisons between some experimental findings and theoretical results are performed to test the reliability of the calculation method preferred in the study. The comparison results in high correlation parameters such as R2 =0.976 and R2 =0.985 for the molecular structures and vibrational frequencies in the DFT and HF calculation levels, respectively. Moreover, the obtained vibrational frequencies and calculated results are in good agreement with the experimental data. Additionally, the simulations of highest/lowest occupied/unoccupied molecular orbital (HOMO and LUMO), molecular electrostatic potential (MEP), and electrostatic potential (ESP) maps have shown that there appear strong non-uniform intra-molecular charge distributions (ICT), electron engagements, lone pairs of electrons, π-π* conjugative effects based on the bond weakening, and intermolecular hydrogen bonding in the compound. Correspondingly, the molecule with the electrophilic reactive and nucleophilic regions has been noted to exhibit kinetical chemical stability. All the discussions have been confirmed by means of the findings of optimized molecular structures and vibrational frequencies belonging to the molecule.

Keywords

N-(4-dimethylamino 3, 5-dinitrophenyl)maleimide, DFT-HF calculations, HOMO and LUMO, MEP, Molecular structure

References

Y. Durust, H. Karakus, M. Kaiser, D. Tasdemir, Synthesis and anti-protozoal activity of novel dihydropyrrolo [3,4-d] [1,2,3]triazoles, European Journal of Medicinal Chemistry (48) (2012) 296–304.
N. Acero, M. F. Brana, L. Anorbe, G. Dominguez, D. Munoz-MIngarro, F. Mitjans, J. Piulat, Synthesis and biological evaluation of novel indolocarbazoles with antiangiogenic activity, European Journal of Medicinal Chemistry (48) (2012) 108–113.
S. N. Lopez, M. Sortino, A. Escalante, F. Campos, R. Correa, V. Cechinel-Filho, R. J. Nunes, S. A. Zacchino, Antifungal properties of novel N- and alpha, beta-substituted succinimides against dermatophytes, Arzneimittel-Forschung/Drug Research (53) (2003) 280–288.
R. Badru, P. Anand, B. Singh, Synthesis and evaluation of hexahydropyrrolo [3,4-d] isoxazole-4,6-diones as anti-stress agents, European Journal of Medicinal Chemistry (48) (2012) 81–91.
A. Ereeg, R. Vukovic, G. Bogdanic, D. Fles, Free-radical-initiated copolymerization of 2,6-dichlorostyrene with maleimide, n-methylmaleimide and n-phenylmaleimide, Journal of Macromolecular Science Part A Pure and Applied Chemistry, A37 (5) (2000) 513-524.
D. Fles, R. Vukovic, Free-radical-initiated polymerization of 6-maleimidocholesterylhexanoate and 4-maleimidocholesterylbenzoate and copolymerization with α-methylstyrene, Journal of Macromolecular Science Part A Pure and Applied Chemistry 32 (8-9) (1995) 1461-1472.
N. Matuszak, G. Muccioli, G. Laber, D. Lambert, Synthesis and in vitro evaluation of n-substituted maleimide derivatives as selective monoglyceride lipase inhibitors, Journal of Medicinal Chemistry 52 (23) (2009) 7410–7420.
J. R. Cashman, M. MacDonald, S. Ghirmai, K. J. Okolotowicz, E. Serienko, B. Brown, X. Garcio, D. Zhai, R. Dahl, J. C. Reed, Inhibition of Bfl-1 with n-aryl maleimides, Bioorganic & Medicinal Chemistry 20 (22) (2010) 6560–6564.
T. Suzuki, R. Tanaka, S. Hamada, H. Nakagawa, N. Miyata, Design, synthesis, inhibitory activity, and binding mode study of novel DNA methyltransferase inhibitors, Bioorganic & Medicinal Chemistry (20) (2010) 1124–1127.
M. Sortino, F. Garibotto, V. Cechinel Filho, M. Gupta, R. Enriz, S. Zacchino, Antifungal, cytotoxic and SAR studies of a series of N-alkyl, N-aryl and N-alkyl phenyl-1, 4-pyrrolidones and related compounds, Bioorganic & Medicinal Chemistry (19) (2011) 2823–2834.

N. Salewska, J. Boro-Majewka, I. Lacka, K. Chylinska, M. Sabisz, S. Milewski, M. J. Milewska, Chemical reactivity and antimicrobial activity of N-substituted maleimides, Journal of Enzyme Inhibition and Medicinal Chemistry 27 (1) (2012) 117–124.
H. H. Wu, P. P. Chu, Structure characteristics contributing to flame retardancy in diazo modified novolac resins, Polymer Degradation and Stability (94) (2009) 987-995.
T. D. Kim, H. J. Ryu, H. I. Cho, C. H. Yang, J. Kim, Thermal behavior of proteins: heat-resistant proteins and their heat-induced secondary structural changes, Biochemistry (39) (2000) 14839-14846.
J. R. Durig, A. Ganguly, A. M. El Defrawy, G. A. Guirgis, T. K. Gounev, W. A. Herrebout, B. J. Van der veken, Conformational stability, r0 structural parameters, barriers to internal rotation and vibrational assignment of cyclobutylamine, Journal of Molecular Structure 918 (1-3) (2009) 64–76.
Y. X. Sun, Q. L. Hao, L. D. Lu, X. Wang, X. J. Yang, Vibrational spectroscopic study of o-, m- and p-hydroxybenzylideneaminoantipyrines, Spectrochimica Acta Part A: Molecular and Biomolecular Spectroscopy (75) (2010) 203–211.
Spectral Database for Organic Compounds, https://sdbs.db.aist.go.jp/sdbs/cgi-bin/direct_frame_top.cgi, Accessed 28.01.2023.
M. J. Frisch, G. W. Trucks, H. B. Schlegel, G. E. Scuseria, M. A. Robb, J. R. Cheeseman, G. Scalmani, V. Barone, B. Mennucci, G. A. Petersson, H. Nakatsuji, M. Caricato, X. Li, H. P. Hratchian, A. F. Izmaylov, J. Bloino, G. Zheng, J. L. Sonnenberg, M. Hada, M. Ehara, K. Toyota, R. Fukuda, J. Hasegawa, M. Ishida, T. Nakajima, Y. Honda, O. Kitao, H. Nakai, T. Vreven, J. A. Montgomery, Jr., J. E. Peralta, F. Ogliaro, M. Bearpark, J. J. Heyd, E. Brothers, K. N. Kudin, V. N. Staroverov, R. Kobayashi, J. Normand, K. Raghavachari, A. Rendell, J. C. Burant, S. S. Iyengar, J. Tomasi, M. Cossi, N. Rega, J. M. Millam, M. Klene, J. E. Knox, J. B. Cross, V. Bakken, C. Adamo, J. Jaramillo, R. Gomperts, R. E. Stratmann, O. Yazyev, A. J. Austin, R. Cammi, C. Pomelli, J. W. Ochterski, R. L. Martin, K. Morokuma, V. G. Zakrzewski, G. A. Voth, P. Salvador, J. J. Dannenberg, S. Dapprich, A. D. Daniels, O. Farkas, J. B. Foresman, J. V. Ortiz, J. Cioslowski, D. J. Fox, Gaussian, Inc., Wallingford, CT, 2009.
R. Dennington II, T. Keith, J. Millam, GaussView, Version 4.1.2, Semichem, Inc., Shawnee Mission, KS, 2007.
A. Saiardi, H. Erdjument-Bromage, A. M. Snowman, P. Tempst, S. H. Snyder, Synthesis of diphosphoinositol pentakisphosphate by a newly identified family of higher inositol polyphosphate kinases, Current Biology (9) (1999) 1323–1326.
S. M. Voglmaier, M. E. Bembenek, A. E. Kaplin, G. Dormán, J. D. Olszewski, G.D. Prestwich, S.H. Snyder, Purified inositol hexakisphosphate kinase is an ATP synthase: diphosphoinositol pentakisphosphate as a high-energy phosphate donor, Proceedings of the National Academy of Sciences of the United States of America (93) (1996) 4305–4310.
A. Saiardi, E. Nagata, H. R. Luo, A. M. Snowman, S. H. Snyder, Identification and characterization of a novel inositol hexakisphosphate kinase, Journal of Biological Chemistry (276) (2001) 39179–39185.
M. J. Schell, A. J. Letcher, C. A. Brearley, J. Biber, H. Murer, R. F. Irvine, PiUS (Pi uptake stimulator) is an inositol hexakisphosphate kinase, FEBS Letters (461) (1999) 169–172.
E. B. Wilson, J. C. Decius, P. C. Cross, Molecular Vibrations: The Theory of Infrared and Raman Vibrational Spectra, Dover Publication Inc., New York, 1980.
P.W. Atkins, R. S. Friedman, Molecular Quantum Mechanics, 3rd edition, Dover Publication Inc., New York, 1996.
H. Gökce, S. Bahçeli, A study of molecular structure and vibrational spectra of copper (ii) halide complex of 2-(2′-thienyl)pyridine, Journal of Molecular Structure (1005) (2011) 100-106.
U. Ceylan, G. Ozdemir Tarı, H. Gökce, E. Agar, Spectroscopic (FT-IR and UV-Vis) and theoretical (HF and DFT) investigation of 2-Ethyl-N- [(5-nitrothiophene-2-yl)methylidene] aniline, Journal of Molecular Structure (1110) (2016) 1-10.
M. Karabacak, M. Kurt, M. Cinar, A. Coruh, Experimental (UV, NMR, IR and Raman) and theoretical spectroscopic properties of 2-chloro-6-methylaniline, Molecular Physics (107) (2009) 253-264.
N. Sundaraganesan, S. Ilakiamani, H. Saleem, P. M. Wojciechowski, D. Michalska, FT-Raman and FT-IR spectra, vibrational assignments and density functional studies of 5-bromo-2-nitropyridine, Spectrochimica Acta Part A: Molecular and Biomolecular Spectroscopy (61) (2004) 2995-3001.
J. Coates, Interpretation of Infrared Spectra: A Practical Approach, John Wiley & Sons Inc., New York, 2000.
N. P. G. Roeges, A Guide to Complete Interpretation of Infrared Spectra of Organic Structures, John Wiley & Sons Inc., New York, 1994.
T. D. Klots, W. B. Collier, Heteroatom derivatives of indene Part 3. vibrational spectra of benzoxazole, benzofuran, and indole, Spectrochimica Acta Part A: Molecular and Biomolecular Spectroscopy (51) (1995) 1291-1316.
G. Varsányi, Assignments for vibrational spectra of seven hundred benzene derivatives, Halsted Press, 1974.
L. J. Bellamy, The Infrared Spectra of Complex Molecules, John Wiley & Sons Inc., New York, 1975.
R. Silverstein, F. Webster, Spectroscopic Identification of Organic Compounds, John Wiley & Sons, New York. 1997.
Y. Sert, F. Ucun, G. A. El-Hiti, K. Smith, A. S. Hegazy, Spectroscopic investigations and DFT calculations on 3-(diacetylamino)-2-ethyl-3H-quinazolin-4-one, Journal of Spectroscopy (7) (2016) 1-15.
S. Pinchas, D. Samuel, M. Weiss-Broday, The infrared absorption of 18O-labelled benzamide, Journal of Chemical Society (1) (1961) 1688-1689.
M. Tsuboi, 15 N isotope effects on the vibrational frequencies of aniline and assignments of the frequencies of its nh2 group, Spectrochimica Acta (16) (1960) 505-512.
B. Wojtkowaik, M. Chabanel, Spectrochimie Moleculaire Technique et Documentation, Paris, 1977.
H. Baraistka, A. Labudzinska, J. Terpinski, Laser Raman Spectroscopy: Analytical Applications, PWN Polish Scientific Publishers/Ellis Harwood Limited Publishers, 1987.
L. Rintoul, A. S. Micallef, S. E. Bottle, The vibrational group frequency of the N–Oradical dot stretching band of nitroxide stable free radicals, Spectrochimica Acta Part A: Molecular and Biomolecular Spectroscopy (70) (2008) 713-717.
S. Subashchandrabose, H. Saleem, Y. Erdogdu, O. Dereli, V. Thanikachalam, J. Jayabharathi, Structural, vibrational and hyperpolarizability calculation of (E)-2-(2-hydroxybenzylideneamino)-3-methylbutanoic acid, Spectrochimica Acta Part A: Molecular and Biomolecular Spectroscopy (86) (2012) 231-241.
F. Karaboga, U. Soykan, M. Dogruer, B. Ozturk, G. Yildirim, S. Cetin, C. Terzioglu, Experimental and theoretical approaches for identification of p-benzophenoneoxycarbonylphenyl acrylate, Spectrochimica Acta Part A: Molecular and Biomolecular Spectroscopy (113) (2013) 80-91.
N. Tezer, N. Karakus, Theoretical study on the ground state intramolecular proton transfer (IPT) and solvation effect in two Schiff bases formed by 2-aminopyridine with 2-hydroxy-1-naphthaldehyde and 2-hydroxy salicylaldehyde, Journal of Molecular Modeling (15) (2009) 223-232.
J. Z. Zhang, G. Y. Zhao, R. Z. Li, D.Y. Hou, Time-dependent density functional theory study on the electronic excited state of hydrogen-bonded clusters formed by 2-hydroxybenzonitrile (o-cyanophenol) and carbon monoxide, Journal of Cluster Science (22) (2011) 501-511.
D. C. Lee, Y. Jeong, L.V. Brownell, J. E. Velasco, K. A. Robins, Y. Lee, Theory guided systematic molecular design of benzothiadiazole-phenazine based self-assembling electron-acceptors, Royal Society of Chemistry Advances (7) (2017) 24105-24112.
N. Castillo, R. J. Boyd, A theoretical study of the fluorine valence shell in methyl fluoride, Chemical Physics Letters (403) (2005) 47-54.
J. Olsen, P. J. Jørgensen, Linear and non-linear response functions for an exact state and for an MCSCF state, The Journal of Chemical Physics (82) (1985) 3235–3264.
T. U. Helgaker, H. J. A. Jensen, P.J. Jørgensen, Analytical calculation of MCSCF dipole‐moment derivatives, Chemical Physics (84) (1986) 6280–6287.
Y. X. Sun, W. X. Wei, Q. L. Hao, L. D. Lu, X. Wang, Experimental and theoretical studies on 4-(2,4-dichlorobenzylideneamino)antipyrine and 4-(2,6-dichlorobenzylideneamino)antipyrine, Spectrochimica Acta Part A: Molecular and Biomolecular Spectroscopy 73(4) (2009) 772-781.
J. B. Foresman, A. Frisch, Exploring Chemistry with Electronic Structure Methods, Gaussian Inc., Pittsburgh, PA, 1996.
G. Gece, The use of quantum chemical methods in corrosion inhibitor studies, Corrosion Science (50) (2008) 2981-2992.
K. Fukui, Role of frontier orbitals in chemical reactions, Science (218) (1987) 747-754.
D. F. V. Lewis, C. Ioannides, D. V. Parke, Interaction of a series of nitriles with the alcohol-inducible isoform of p450: computer analysis of structure activity relationships, Xenobiotica (24) (1994) 401-408.
N. Ozdemir, B. Eren, M. Dincer, Y. Bekdemir, Experimental and ab initio computational studies on 4-(1hbenzo [d]imidazol-2-yl)-n,n-dimethylaniline, Molecular Physics (108) (2010) 13–24.
P. Politzer, J. S. Murray, The fundamental nature and role of the electrostatic potential in atoms and molecules, Theoretical Chemistry Accounts (108) (2002) 134–142.
F. J. Luque, J. M. Lopez, M. Orozco, Electrostatic interactions of a solute with a continuum. A direct utilization of ab initio molecular potentials for the prevision of solvent effects, Theoretical Chemistry Accounts (103) (2000) 343–345.
N. Okulik, A. H. Joubert, Theoretical analysis of the reactive sites of non-steroidal anti-inflammatory drugs, Internet Electronic Journal of Molecular Design (4) (2005) 17–30.
D. L. Wang, X. P. Sun, H. T. Shen, D. Y. Hou, Y. C. Zhai, A comparative study of the electrostatic potential of fullerene-like structures of Au32 and Au42, Journal of Chemical Physics Letter (457) (2008) 366–370.

Details

Primary Language

English

Subjects

-

Journal Section

Research Article

Authors

Seda Karaboğa ^*
0000-0003-2681-382X
Türkiye

Gürcan Yıldırım
0000-0002-5177-3703
Türkiye

Publication Date

April 30, 2023

Submission Date

January 23, 2023

Acceptance Date

April 12, 2023

Published in Issue

Year 2023 Volume: 12 Number: 1

DOI

https://doi.org/10.54187/jnrs.1241130

IZ

https://izlik.org/JA97BK68LM

APA

Karaboğa, S., & Yıldırım, G. (2023). A comparative investigation for identification of N-(4-dimethylamino 3,5-dinitrophenyl)maleimide. Journal of New Results in Science, 12(1), 27-46. https://doi.org/10.54187/jnrs.1241130

AMA

1.Karaboğa S, Yıldırım G. A comparative investigation for identification of N-(4-dimethylamino 3,5-dinitrophenyl)maleimide. JNRS. 2023;12(1):27-46. doi:10.54187/jnrs.1241130

Chicago

Karaboğa, Seda, and Gürcan Yıldırım. 2023. “A Comparative Investigation for Identification of N-(4-Dimethylamino 3,5-Dinitrophenyl)maleimide”. Journal of New Results in Science 12 (1): 27-46. https://doi.org/10.54187/jnrs.1241130.

EndNote

Karaboğa S, Yıldırım G (April 1, 2023) A comparative investigation for identification of N-(4-dimethylamino 3,5-dinitrophenyl)maleimide. Journal of New Results in Science 12 1 27–46.

IEEE

[1]S. Karaboğa and G. Yıldırım, “A comparative investigation for identification of N-(4-dimethylamino 3,5-dinitrophenyl)maleimide”, JNRS, vol. 12, no. 1, pp. 27–46, Apr. 2023, doi: 10.54187/jnrs.1241130.

ISNAD

Karaboğa, Seda - Yıldırım, Gürcan. “A Comparative Investigation for Identification of N-(4-Dimethylamino 3,5-Dinitrophenyl)maleimide”. Journal of New Results in Science 12/1 (April 1, 2023): 27-46. https://doi.org/10.54187/jnrs.1241130.

JAMA

1.Karaboğa S, Yıldırım G. A comparative investigation for identification of N-(4-dimethylamino 3,5-dinitrophenyl)maleimide. JNRS. 2023;12:27–46.

MLA

Karaboğa, Seda, and Gürcan Yıldırım. “A Comparative Investigation for Identification of N-(4-Dimethylamino 3,5-Dinitrophenyl)maleimide”. Journal of New Results in Science, vol. 12, no. 1, Apr. 2023, pp. 27-46, doi:10.54187/jnrs.1241130.

Vancouver

1.Seda Karaboğa, Gürcan Yıldırım. A comparative investigation for identification of N-(4-dimethylamino 3,5-dinitrophenyl)maleimide. JNRS. 2023 Apr. 1;12(1):27-46. doi:10.54187/jnrs.1241130